19353-89-0Relevant articles and documents
Ligand-Enabled Nickel-Catalyzed Redox-Relay Migratory Hydroarylation of Alkenes with Arylborons
He, Yuli,Liu, Chuang,Yu, Lei,Zhu, Shaolin
supporting information, p. 9186 - 9191 (2020/04/30)
A redox-relay migratory hydroarylation of isomeric mixtures of olefins with arylboronic acids catalyzed by nickel complexes bearing diamine ligands is described. A range of structurally diverse 1,1-diarylalkanes, including those containing a 1,1-diarylated quaternary carbon, were obtained in excellent yields and with high regioselectivity. Preliminary experimental evidence supports the proposed non-dissociated chainwalking of aryl-nickel(II)-hydride species along the alkyl chain of alkenes before selective reductive elimination at a benzylic position. A catalyst loading as low as 0.5 mol % proved to be sufficient in large-scale synthesis while retaining high reactivity, highlighting the practical value of this transformation.
Synthesis of 1-aryl- benzocycloalkane derivatives via one-pot two-step reaction of benzocyclonone, tosylhydrazide, and arylboronic acid
Liu, Shijuan,Fang, Meitong,Yin, Dongni,Wang, Yanan,Liu, Lei,Li, Xiuying,Che, Guangbo
, p. 942 - 949 (2019/03/14)
A metal-free one-pot two-step reductive coupling reaction of benzocyclonone, tosylhydrazide, and arylboronic acid was developed for the formation of a C(sp3)–C(sp2) bond, which enabled the efficient synthesis of 1-aryl-benzocycloalkane compounds in moderate to good yields on a multi-gram scale. Moreover, five- and six-membered benzocyclic ketones are also suitable substrates for this reaction. Notably, this protocol was also found to be suitable for synthesizing 3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-one, an important intermediate in the synthesis of indatraline.
Effect of methoxyl groups on the NMR spectra: configuration and conformation of natural and synthetic indanic and tetralinic structures
Lanta?o, Beatriz,Aguirre, José M.,Drago, Eleonora V.,de la Faba, Diego J.,Pomilio, Nicolás,Mufato, Jorge D.
, p. 619 - 633 (2017/06/08)
Here, we studied the influence of the methoxyl groups attached at C-7 and C-2′ of natural and synthetic 1-arylindanes on the chemical shift of the signal of bibenzylic hydrogen and carbon atoms and J1,2 coupling constants. This influence was also analysed in natural 1-aryltetralins and related compounds that possess methoxyl and/or hydroxyl groups bound at C-8 and C-2′. The methoxyl groups attached at C-7 in indanes or at C-8 in tetralins produce a deshielding signal at H-1 and shield at C-1 and a strong decrease in the value of J1,2 due to the pseudoequatorial location adopted by the aryl group bound at C-1, avoiding an ‘A1,3 strain’. Furthermore, compounds with hydroxyl or methoxyl groups in C-2′, in the absence of substituents of C-7 or C-8, present a strong deshielding signal at H-1, strong shield of the C-1 signal and a decrease in the value of J1,2. This is attributed to the stereoelectronic effects of the methoxyl or hydroxyl groups, which we have called ‘Asarone effect’. NOESY experiments were conducted to confirm the configuration and conformation of some of the compounds included in this work. This study shows that both effects, A1,3 strain and Asarone effect, must be taken into account when the structure of natural indanes and tetralins is analysed by using 1H-NMR and 13C-NMR spectra. Copyright
Remote migratory cross-electrophile coupling and olefin hydroarylation reactions enabled by in situ generation of nih
Chen, Fenglin,Chen, Ke,Zhang, Yao,He, Yuli,Wang, Yi-Ming,Zhu, Shaolin
supporting information, p. 13929 - 13935 (2017/11/07)
A highly efficient strategy for remote reductive cross-electrophile coupling has been developed through the ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1, 1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0 as a potential hydride source.
Mild and regioselective benzylic C-H functionalization: Ni-catalyzed reductive arylation of remote and proximal olefins
He, Yuli,Cai, Yalei,Zhu, Shaolin
supporting information, p. 1061 - 1064 (2017/05/15)
The synergistic combination of NiH-catalyzed alkene isomerization with nickel-catalyzed cross-coupling has yielded a general protocol for the synthesis of a wide range of structurally diverse 1,1-diarylalkanes in excellent yields and high regioselectivities from readily accessible olefin starting materials. Furthermore, the practicality and synthetic flexibility of this approach is highlighted by the successful employment of isomeric mixtures of olefins for regioconvergent arylation.
Room Temperature Catalyst System for the Hydroarylation of Olefins
Lee, Siu Yin,Villani-Gale, Alexander,Eichman, Chad C.
supporting information, p. 5034 - 5037 (2016/10/14)
A simple protocol for the hydroarylation of olefins to yield diarylmethine products is described. A Friedel-Crafts-type synthetic strategy allows direct access to biorelevant products in high atom efficiency. A combination of substoichiometric amounts of TMSCl and ZnBr2 promotes a rapid hydroarylation process at ambient temperature. The method is high yielding and is amenable to scale-up protocols.
Cu-catalyzed intramolecular hydroarylation of alkynes
Wang, Yun-Long,Zhang, Wen-Man,Dai, Jian-Jun,Feng, Yi-Si,Xu, Hua-Jian
, p. 61706 - 61710 (2015/02/19)
An efficient Cu-catalyzed intramolecular hydroarylation reaction of alkynes has been developed. The reaction is accomplished under mild conditions and shows good tolerance to both electron-rich and electron-deficient aryl nucleophiles. A series of aryl, h
Cationic Iron(III) porphyrin catalyzed dehydrative friedel-crafts reaction of alcohols with arenes
Teranishi, Satoru,Kurahashi, Takuya,Matsubara, Seijiro
supporting information, p. 2148 - 2152 (2013/10/21)
Alcohols react with arenes in the presence of cationic iron(III) porphyrin catalyst. The reaction involves the formation of the C-C bond via dehydration, which is formal Lewis acid catalyzed Friedel-Crafts reaction. Georg Thieme Verlag Stuttgart, New York.
Cross-coupling of grignard reagents with sulfonyl-activated sp3 carbon-nitrogen bonds
Li, Man-Bo,Tang, Xiang-Ling,Tian, Shi-Kai
, p. 1980 - 1984 (2011/10/12)
Sulfonyl-activated sp3 carbon-nitrogen bonds have been found to be cleaved by Grignard reagents in the presence of 5 mol% of copper(I) iodide (CuI). Significantly, a broad range of sulfonyl-activated benzylic, allylic, and propargylic amines smoothly undergo the cross-coupling reaction with Grignard reagents to afford structurally diverse coupling products in good to excellent yields and with high chemo-, regio-, and stereoselectivity. Moreover, an S N2 mechanism has been demonstrated to be involved in the cross-coupling reaction that allows the asymmetric synthesis of chiral hydrocarbons from optically active α-branched amine derivatives. Copyright
Efficient and general continuous-flow hydroarylation and hydroalkylation of styrenes
Rueping, Magnus,Bootwicha, Teerawut,Sugiono, Erli
experimental part, p. 2961 - 2965 (2011/02/22)
A simple and efficient continuous-flow hydroarylation of arenes and heteroarenes using various styrenes in conjunction with a heterogeneous catalyst has been developed. Additionally, this method has been successfully extended to the hydroalkylation of styrenes by employing 1,3-dicarbonyl compounds as the nucleophile. Multigram quantities of diarylmethanes have been prepared using this new flow method. Copyright
